TWI321558B - - Google Patents

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Info

Publication number: TWI321558B
Authority: TW; Taiwan
Prior art keywords: concentration; amine; hydroxylamine; tower; cyclohexanone
Prior art date: 2007-01-05

Application number

TW096100436A

Other languages

English (en)

Chinese (zh)

Other versions

TW200829544A (en

Inventor

Jih Dar Hwang

Kai Hung Haung

Hsiu Li Cheng

Shou Li Luo

Original Assignee

China Petrochemical Dev Corp

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2007-01-05

Filing date

2007-01-05

Publication date

2010-03-11

2007-01-05 Application filed by China Petrochemical Dev Corp filed Critical China Petrochemical Dev Corp

2007-01-05 Priority to TW096100436A priority Critical patent/TW200829544A/zh

2007-11-20 Priority to US11/986,366 priority patent/US7671236B2/en

2007-12-20 Priority to PL07150260T priority patent/PL1942099T3/pl

2007-12-20 Priority to ES07150260T priority patent/ES2340623T3/es

2007-12-20 Priority to DE602007004935T priority patent/DE602007004935D1/de

2007-12-20 Priority to EP07150260A priority patent/EP1942099B1/en

2007-12-20 Priority to AT07150260T priority patent/ATE458716T1/de

2008-07-16 Publication of TW200829544A publication Critical patent/TW200829544A/zh

2010-03-11 Application granted granted Critical

2010-03-11 Publication of TWI321558B publication Critical patent/TWI321558B/zh

Links

JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims abstract description 55
238000000034 method Methods 0.000 claims abstract description 51
HYYHQASRTSDPOD-UHFFFAOYSA-N hydroxylamine;phosphoric acid Chemical compound ON.OP(O)(O)=O HYYHQASRTSDPOD-UHFFFAOYSA-N 0.000 claims abstract description 29
230000008569 process Effects 0.000 claims abstract description 29
VEZUQRBDRNJBJY-UHFFFAOYSA-N cyclohexanone oxime Chemical compound ON=C1CCCCC1 VEZUQRBDRNJBJY-UHFFFAOYSA-N 0.000 claims abstract description 22
238000002156 mixing Methods 0.000 claims abstract description 3
238000006243 chemical reaction Methods 0.000 claims description 36
239000007788 liquid Substances 0.000 claims description 27
150000001412 amines Chemical class 0.000 claims description 26
239000002253 acid Substances 0.000 claims description 13
239000012295 chemical reaction liquid Substances 0.000 claims description 13
239000012074 organic phase Substances 0.000 claims description 12
238000004519 manufacturing process Methods 0.000 claims description 11
YPHMISFOHDHNIV-FSZOTQKASA-N cycloheximide Chemical compound C1[C@@H](C)C[C@H](C)C(=O)[C@@H]1[C@H](O)CC1CC(=O)NC(=O)C1 YPHMISFOHDHNIV-FSZOTQKASA-N 0.000 claims description 10
238000010297 mechanical methods and process Methods 0.000 claims description 8
230000005226 mechanical processes and functions Effects 0.000 claims description 8
239000000126 substance Substances 0.000 claims description 8
239000003960 organic solvent Substances 0.000 claims description 4
UROFTPKQEUJFCY-UHFFFAOYSA-N C1CC[CH-]CC1 Chemical group C1CC[CH-]CC1 UROFTPKQEUJFCY-UHFFFAOYSA-N 0.000 claims description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 2
239000001117 sulphuric acid Substances 0.000 claims description 2
235000011149 sulphuric acid Nutrition 0.000 claims description 2
NAQGQNNLOQOFNT-UHFFFAOYSA-N NO.[P] Chemical compound NO.[P] NAQGQNNLOQOFNT-UHFFFAOYSA-N 0.000 claims 1
ICTGZZCWICGWMG-UHFFFAOYSA-N NO.[S] Chemical compound NO.[S] ICTGZZCWICGWMG-UHFFFAOYSA-N 0.000 claims 1
238000000746 purification Methods 0.000 claims 1
238000006146 oximation reaction Methods 0.000 abstract 4
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 16
239000000243 solution Substances 0.000 description 16
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 12
230000000052 comparative effect Effects 0.000 description 10
238000000605 extraction Methods 0.000 description 9
-1 cyclohexanyl Chemical group 0.000 description 8
206010036790 Productive cough Diseases 0.000 description 7
230000007246 mechanism Effects 0.000 description 7
210000003802 sputum Anatomy 0.000 description 7
208000024794 sputum Diseases 0.000 description 7
HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 6
239000000463 material Substances 0.000 description 6
239000005416 organic matter Substances 0.000 description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
229910002651 NO3 Inorganic materials 0.000 description 5
NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 5
238000010521 absorption reaction Methods 0.000 description 5
239000001257 hydrogen Substances 0.000 description 5
229910052739 hydrogen Inorganic materials 0.000 description 5
NBIIXXVUZAFLBC-UHFFFAOYSA-N phosphoric acid Substances OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 5
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 4
JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
208000001613 Gambling Diseases 0.000 description 3
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 3
229910000147 aluminium phosphate Inorganic materials 0.000 description 3
229910052797 bismuth Inorganic materials 0.000 description 3
JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 description 3
238000010586 diagram Methods 0.000 description 3
229910017604 nitric acid Inorganic materials 0.000 description 3
239000002904 solvent Substances 0.000 description 3
229910019142 PO4 Inorganic materials 0.000 description 2
KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 2
TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
230000008859 change Effects 0.000 description 2
239000007789 gas Substances 0.000 description 2
GDOPTJXRTPNYNR-UHFFFAOYSA-N methylcyclopentane Chemical compound CC1CCCC1 GDOPTJXRTPNYNR-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
239000010452 phosphate Substances 0.000 description 2
230000004044 response Effects 0.000 description 2
229910052707 ruthenium Inorganic materials 0.000 description 2
VZXTWGWHSMCWGA-UHFFFAOYSA-N 1,3,5-triazine-2,4-diamine Chemical compound NC1=NC=NC(N)=N1 VZXTWGWHSMCWGA-UHFFFAOYSA-N 0.000 description 1
235000010254 Jasminum officinale Nutrition 0.000 description 1
240000005385 Jasminum sambac Species 0.000 description 1
KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 1
239000004472 Lysine Substances 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
229910000831 Steel Inorganic materials 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
239000006096 absorbing agent Substances 0.000 description 1
239000011449 brick Substances 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
238000005660 chlorination reaction Methods 0.000 description 1
239000000356 contaminant Substances 0.000 description 1
125000004122 cyclic group Chemical group 0.000 description 1
125000002243 cyclohexanonyl group Chemical group *C1(*)C(=O)C(*)(*)C(*)(*)C(*)(*)C1(*)* 0.000 description 1
XMAMHMFNHBBMMI-UHFFFAOYSA-N cyclohexene;toluene Chemical compound C1CCC=CC1.CC1=CC=CC=C1 XMAMHMFNHBBMMI-UHFFFAOYSA-N 0.000 description 1
IGARGHRYKHJQSM-UHFFFAOYSA-N cyclohexylbenzene Chemical compound C1CCCCC1C1=CC=CC=C1 IGARGHRYKHJQSM-UHFFFAOYSA-N 0.000 description 1
230000000694 effects Effects 0.000 description 1
238000005516 engineering process Methods 0.000 description 1
238000000855 fermentation Methods 0.000 description 1
230000004151 fermentation Effects 0.000 description 1
238000002309 gasification Methods 0.000 description 1
238000006703 hydration reaction Methods 0.000 description 1
239000012535 impurity Substances 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
239000011259 mixed solution Substances 0.000 description 1
239000000203 mixture Substances 0.000 description 1
WSGCRAOTEDLMFQ-UHFFFAOYSA-N nonan-5-one Chemical compound CCCCC(=O)CCCC WSGCRAOTEDLMFQ-UHFFFAOYSA-N 0.000 description 1
239000002957 persistent organic pollutant Substances 0.000 description 1
239000012071 phase Substances 0.000 description 1
JTJMJGYZQZDUJJ-UHFFFAOYSA-N phencyclidine Chemical compound C1CCCCN1C1(C=2C=CC=CC=2)CCCCC1 JTJMJGYZQZDUJJ-UHFFFAOYSA-N 0.000 description 1
238000004064 recycling Methods 0.000 description 1
230000009467 reduction Effects 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
239000010959 steel Substances 0.000 description 1
229910021653 sulphate ion Inorganic materials 0.000 description 1
239000013589 supplement Substances 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C249/00—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C249/04—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton of oximes
- C07C249/08—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton of oximes by reaction of hydroxylamines with carbonyl compounds
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

TW096100436A 2007-01-05 2007-01-05 Method for preparing cyclohexanone oxime TW200829544A (en)

Priority Applications (7)

Application Number	Priority Date	Filing Date	Title
TW096100436A TW200829544A (en)	2007-01-05	2007-01-05	Method for preparing cyclohexanone oxime
US11/986,366 US7671236B2 (en)	2007-01-05	2007-11-20	Process for production of cyclohexanone oxime
PL07150260T PL1942099T3 (pl)	2007-01-05	2007-12-20	Sposób wytwarzania oksymu cykloheksanonu
ES07150260T ES2340623T3 (es)	2007-01-05	2007-12-20	Procedimiento para la produccion de ciclohexanonixima.
DE602007004935T DE602007004935D1 (de)	2007-01-05	2007-12-20	Verfahren zur Herstellung von Cyclohexanon-Oxim
EP07150260A EP1942099B1 (en)	2007-01-05	2007-12-20	Process for production of cyclohexanone oxime
AT07150260T ATE458716T1 (de)	2007-01-05	2007-12-20	Verfahren zur herstellung von cyclohexanon-oxim

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
TW096100436A TW200829544A (en)	2007-01-05	2007-01-05	Method for preparing cyclohexanone oxime

Publications (2)

Publication Number	Publication Date
TW200829544A TW200829544A (en)	2008-07-16
TWI321558B true TWI321558B (pl)	2010-03-11

Family

ID=39263297

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
TW096100436A TW200829544A (en)	2007-01-05	2007-01-05	Method for preparing cyclohexanone oxime

Country Status (7)

Country	Link
US (1)	US7671236B2 (pl)
EP (1)	EP1942099B1 (pl)
AT (1)	ATE458716T1 (pl)
DE (1)	DE602007004935D1 (pl)
ES (1)	ES2340623T3 (pl)
PL (1)	PL1942099T3 (pl)
TW (1)	TW200829544A (pl)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US9382195B2 (en) *	2013-03-14	2016-07-05	Honeywell International Inc.	Oximation of KA oil by-product
TWI620733B (zh) *	2013-05-21	2018-04-11	拜耳作物科學股份有限公司	製備特定肟類及肟醚類之改良方法
CN110423206B (zh) *	2019-07-17	2022-07-08	天津大学	从氨肟化反应产物中分离环己酮肟、环己酮与甲苯的方法

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
NL6513426A (pl) *	1965-10-16	1967-04-17
US3940442A (en) *	1969-12-06	1976-02-24	Stamicarbon B.V.	Recycle process for the preparation and processing of a hydroxylammonium salt solution
BE759914A (fr) *	1969-12-06	1971-06-04	Stamicarbon	Procede de recyclage pour la preparation et la traitement d'unesolutionde sel d'hydroxylammonium
US3997607A (en) *	1974-04-26	1976-12-14	Stamicarbon B.V.	Recycling process for the preparation of cyclohexanone oxime
NL7614456A (nl) *	1976-12-28	1978-06-30	Stamicarbon	Kringloopproces voor de bereiding en verwerking van een hydroxylammoniumzoutoplossing.
MXPA02011961A (es) *	2000-06-05	2003-07-14	Dsm Nv	Procedimiento para la produccion de oxima de ciclohexanona.
DE60118745T2 (de) *	2000-06-05	2006-11-16	Dsm Ip Assets B.V.	Verfahren zur herstellung von cyclohexanonoxim
CN1424306A (zh)	2001-12-13	2003-06-18	中国石油化工股份有限公司巴陵分公司	一种提高肟化反应效率的方法
TW200829542A (en) *	2007-01-05	2008-07-16	China Petrochemical Dev Corp	Hydroxylamine -oximination cycling system

2007
- 2007-01-05 TW TW096100436A patent/TW200829544A/zh unknown
- 2007-11-20 US US11/986,366 patent/US7671236B2/en not_active Expired - Fee Related
- 2007-12-20 AT AT07150260T patent/ATE458716T1/de not_active IP Right Cessation
- 2007-12-20 ES ES07150260T patent/ES2340623T3/es active Active
- 2007-12-20 PL PL07150260T patent/PL1942099T3/pl unknown
- 2007-12-20 EP EP07150260A patent/EP1942099B1/en not_active Not-in-force
- 2007-12-20 DE DE602007004935T patent/DE602007004935D1/de active Active

Also Published As

Publication number	Publication date
PL1942099T3 (pl)	2010-07-30
ES2340623T3 (es)	2010-06-07
EP1942099B1 (en)	2010-02-24
DE602007004935D1 (de)	2010-04-08
TW200829544A (en)	2008-07-16
US20080167496A1 (en)	2008-07-10
US7671236B2 (en)	2010-03-02
ATE458716T1 (de)	2010-03-15
EP1942099A1 (en)	2008-07-09

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